I'm thinking about writing my paper on ibogaine. Ibogaine is an indole alkoloid found in the plant Tabernanthe iboga and is known for its hallucinogenic and anti-addictive properties. Ibogaine has been used to treat addiction to heroin, alcohol, cocaine, methamphetamines, opioids, and nicotine. There are several approaches to the subject that I am debating. One would be the biochemistry involved with the ibogaine's interruption of drug dependence. Another would be to look at the various methods of synthesis of ibogaine or its salt ibogaine hydrochloride. Research on the synthesis would perhaps prove useful as, according to Wikipedia, "A full organic synthesis of ibogaine has been achieved but is too expensive and challenging to produce any commercially significant yield." http://en.wikipedia.org/wiki/Ibogaine -Wikipedia article on ibogaine http://en.wikipedia.org/wiki/Tabernanthe_iboga -Wikipedia article on Tabernanthe iboga [Either the biochemistry of action or synthesis would be excellent - it depends on your interest JCB]
November 5, 2009
Assignment 1
[Full Marks JCB]
The Alkaloids of Tabernanthe iboga. Part III. Isolation Studies
Abstract
Twelve compounds are isolated from the root of the plant Tabernanthe iboga.These are the alkaloids ibogamine, ibogaine, tabernanthine, iboluteine, iboquine, desmethoxyiboluteine, hydroxyindolenine derivatives of ibogaine and ibogamine, voacangine, and the new Tabernanthe alkaloids gabonine, kisantine and kimvuline.
Introduction
The major alkaloids were prepared with high purity. As many minor alkaloids that could be isolated were isolated.
The indole alkaloids ibogaine, tebernanthine, ibogamine and iboluteine have a different methoxy group. Hydroperoxy and hydroxyindolenine derivatives of ibogaine are intermediates of catalytic oxidation of ibogaine. Desmethoxyiboluteine is an oxidation product of ibogamine. Iboluteine and iboquine are products of air oxidation of ibogaine.
The direct crystallization of the total alkaloids yields ibogaine and tabernanthine. Hydrochloric acid added to an acetone solution of the alkaloids yields ibogaine hydrochloride precipitate. Crystallization of the filtrate yields tabernanthine.
The amorphous material remaining contained several minor alkaloids: hydroxyindolenine derivatives of ibogaine and ibogamine in larger amounts, as well as iboluteine, desmethoxyiboluteine, and iboquine. These minor alkaloids may be a result of oxidation.
The relationship between Tabernanthe and Voacanga alkaloids is confirmed by the presence of voacangine in Tabernanthe iboga.
New Tabernanthe iboga alkaloids discovered were gabonine, kisantine and kimvuline. Gabonine, empirical formula C21H28N2O4, is a widely distributed Tabernanthe alkaloid. Gabonine has two methoxyl groups.
Kisantine has an empirical formula of C21H28N2O3. Kisantine has two methoxyl groups.
Kimvuline has an empirical formula of C20H26N2O2. Recrystallization of the mother liquor of crude ibogaine yields kimvuline. Kimvuline has a methoxyl group and a hydroxy group.
The authors thank Mr. B. Korzun and Mr. L. Dorfman and his staff.
Experimental
Ibogaine was extracted from 96.7 kg of Tabernanthe iboga.
The 474 g of crude ibogaine was purified to 259 g of pure ibogaine with a melting point of 152-153 degrees Celsius.
100 g of ibogaine was dissolved into 1000 mL of acetone and 51 mL of aqueous HCL was added dropwise. 108.5 g of ibogaine hydrochloride crystals were filtered off and had a melting point of 299-300 degrees Celsius.
The chromatography of the ibogaine mother liquor material was conducted.
76.5 g of crystalline ibogamine was taken from the cyclohexane eluate. After recrystallization from methanol, the meting point of ibogamine was 162-163 degrees Celsius.
1.5 g of the hydroxyindolenine of ibogamine was taken from the filtrate and had a melting point of 161-163 degrees Celsius, 168-172 degrees Celsius after recrysallization from acetone.
1.5 g of tabernanthine with a melting point of 207-211degrees Celsius was extracted from the crude ibogaine.
0.45 g of tabernantine was put in 5 mL of methylene chloride and 0.30 mL of 1:1 aqueous HCL was added. 0.42 g of tabernanthine hydrochloride was crystallized from water, with a melting point of 275-277 degrees Celsius.
The hydroxyindolenine derivative of ibogaine was formed in a benzene solution of 5 g of the mother liquor. the derivative melted at 123-124 degrees Celsius.
The derivative could be recrystallized from acetone or benzene to yield a melting point of 147-149 degrees Celsius.
Eluting with methylene chloride with 1% methanol yielded 0.04 g of crystals melting at 268-271 degrees Celsius. The crystals are believed to be iboquine based upon the UV and IR absorption.
0.16 g of gabonine was crystallized from the amorphous fraction and had a melting point of 223-226 degrees Celsius.
Kisantine was found in the benzene eluate with a melting point of 236-238 degrees Celsius after crystallization from ethanol.
0.55 g of desmethoxyiboluteine with a melting point of 141 degrees Celsius was taken from the methylene chloride containing 0.25% ethanol.
Iboluteine was separated by paper chromatography and after crystallization from methanol had a melting point of 142 degrees Celsius.
0.65 g of voacangine was extracted from a different sample of Tabernanthe iboga root and after recrystallization from ethanol the melting point was 136-137 degrees Celsius.
The voacangine compound had identical IR and X-ray powder spectrum. The compound also contained kisantine and the hydroxyindolenine derivative of ibogaine.
0.26 g of kimvuline was extracted from the mother liquor material with benzene and recrystallized from methanol then benzene to yield a melting point of 231-232.5 degrees Celsius.
Dickel, D. F., C. L. Holden, R. C. Maxfield, L. E. Paszek, and W. I. Taylor. "The Alkaloids of Tabernanthe iboga. Part III. Isolation Studies." Journal of the American Chemical Society 80.1 (1958): 123-25. Web. 27 Oct. 2009. <http://dx.doi.org/10.1021/ja01534a035>.
October 20, 2009
I'm thinking about writing my paper on ibogaine. Ibogaine is an indole alkoloid found in the plant Tabernanthe iboga and is known for its hallucinogenic and anti-addictive properties. Ibogaine has been used to treat addiction to heroin, alcohol, cocaine, methamphetamines, opioids, and nicotine. There are several approaches to the subject that I am debating. One would be the biochemistry involved with the ibogaine's interruption of drug dependence. Another would be to look at the various methods of synthesis of ibogaine or its salt ibogaine hydrochloride. Research on the synthesis would perhaps prove useful as, according to Wikipedia, "A full organic synthesis of ibogaine has been achieved but is too expensive and challenging to produce any commercially significant yield."http://en.wikipedia.org/wiki/Ibogaine -Wikipedia article on ibogaine
http://en.wikipedia.org/wiki/Tabernanthe_iboga -Wikipedia article on Tabernanthe iboga
[Either the biochemistry of action or synthesis would be excellent - it depends on your interest JCB]
November 5, 2009
Assignment 1
[Full Marks JCB]The Alkaloids of Tabernanthe iboga. Part III. Isolation Studies
Abstract
Introduction
Experimental
Dickel, D. F., C. L. Holden, R. C. Maxfield, L. E. Paszek, and W. I. Taylor. "The Alkaloids of Tabernanthe iboga. Part III. Isolation Studies." Journal of the American Chemical Society 80.1 (1958): 123-25. Web. 27 Oct. 2009. <http://dx.doi.org/10.1021/ja01534a035>.
November 6, 2009
Assignment 3
[Full Marks JCB]Diethyl Ether
melting point
-116 °C ChemSpider MSDS
-116 ºC Alfa Aesar
-177 ºF (-116 Cº) NIOSH
-116.3 ºC (156.85 K) Wikipedia
-116 ºC WolframAlpha
boiling point
34.6 ºC ChemSpider MSDS
33.2 ºC at 760 mmHg ChemSpider Predicted
34.6 ºC Alfa Aesar
94.6 ºF (34.8 ºC) NIOSH
34.6 ºC (307.75 K) Wikipedia
flash point
-40 ºC ChemSpider MSDS
-45 ºC (-49 ºF) Alfa Aesar
-49 ºF (-45 ºC) NIOSH
-45 ºC Wikipedia
-40 ºC WolframAlpha
density
0.734 g/cm³ ChemSpider Predicted
0.715 g/cm³ Alfa Aesar
0.7134 g/cm³ Wikipedia
0.706 g/cm³ at STP WolframAlpha
0.7138 g/cm³ CRC Handbook of Chemistry and Physics entry
vapor pressure
440 mmHg ChemSpider NIOSH
567 mmHg at 25 ºC ChemSpider Predicted
400 mm Hg at 18 C MSDS
1482 mmHg WolframAlpha
8.59 psi at 20 ºC (444 mmHg) Sigma-Aldrich
done - 11/19/09